


Personal

by conceptofzero



Category: Homestuck
Genre: M/M
Language: English
Status: Completed
Published: 2012-08-30
Updated: 2012-08-30
Packaged: 2017-11-13 04:19:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,180
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/499400
Author URL: https://archiveofourown.org/users/conceptofzero/pseuds/conceptofzero
Summary: <blockquote class="userstuff">
              <p>"To Gentlemen of Discretion: I am seeking a handsome man of large stature with proportional assets with whom to find amusement and what may follow. Discretion is a must. Serious inquiries only. Send to address Z 52. Signed, Mister Willing."</p><p>Die's personal ads finally pay off, just not in the way he expected.</p>
            </blockquote>





	Personal

**Author's Note:**

> Written as a birthday present for Stamp.

To Gentlemen of Discretion: I am seeking a handsome man of large stature with proportional assets with whom to find amusement and what may follow. Discretion is a must. Serious inquiries only. Send to address Z 52. Signed, Mister Willing.

To Mister Willing: Saw your ad in the paper. May be what you’re looking for. 6’8”, broad & strong. 9” and girthy. Up for anything, very discrete. Contact me if you’re interested. Your Gentleman of Discretion. 

To Gentleman of Discretion: I was delighted to see your response. You are exactly as I had hoped. I am smaller, perhaps 5’11”, and on the thinner side. My other asset is 6” and slim. I am willing to give/get oral, and prefer to get anal. I am up for some rough play but nothing too physical. Once again I must emphasize that I demand discretion. If you are still interested, then rent a room at the Starlight Motel and send me the number. Signed, Mister Willing.

To Mister Willing: Room 27, key enclosed. Discretion no problem. See you very soon. Your Gentleman of Discretion. 

\--

 

The best thing about the Starlight Motel was that it was easy to see exactly who was there. Parking was out in the open, and there were no easy alleyways to hide in. So, for example, if the Midnight Crew was lying in wait to ambush Die and beat him like they had the other time he hadn’t been so discreet when placing a personal ad, then he would see them ahead of time and be able to leave. 

There’s nobody here right now. The whole lot’s emptying and the only car in sight is the one Die drove in. It’s one of the Felt’s less conspicuous vehicles (the paint is black instead of green, though Scratch still added white and green upholstry) and he parks it near the back. His eyes scan the parking lot, but of the few cars here, he recognizes none as belonging to the Crew. Good. 

Die gets out of the car, wincing at the too-loud sound of the door as it shuts. The lack of alleyways that ensure he won’t be ambushed also serve to reveal him and he hunkers down in his coat, wishing he had something in his wardrobe that wasn’t green. There’s nobody around, as far as he can see, but he scurries all the same, quickly hustling through the parking lot and up the stairs to the second floor. The key’s in his pocket and he keeps his fingers clenched tight around it, like he’s going to lose if he lets go.

Only when he stops outside the hotel room does he let himself pause and sincerely think about what might be waiting for him inside. The last few times have been disappointing; a mix of liars who thought that Die somehow wouldn’t notice they weren’t exactly as big as advertised and one unpleasant visit from the Midnight Crew. While the Gentleman of Discretion sounded good, there was a part of Die who honestly worried he might be too good to be true. 

He pulls the key out and looks at it. Die could turn tail, run back to the car and slink away. But if he leaves, he’s going to spend the rest of his life second-guessing his choice and wondering if the man inside the room was exactly as advertised. He steels himself, sticks the key in and turns. The door unlocks and opens, and Die steps in. 

The hulking man standing on the other end of the room brings to mind Boxcars. Then his brain catches up and Die realizes that it is Hearts Boxcars in the flesh. His hands scramble for his gun and the doorknob at the same time, barely getting his grip on both of them. The gun’s out and pointing at Boxcars, ready to bolt the moment Boxcars takes a step toward him. 

Boxcars just sort of nods to himself, as if this just confirmed something. “I figured Mister Willing was you. You kept changing your name, but your demands were pretty distinctive.” 

“What?” The word spills out of his mouth and the gun drops a little, caught off guard by the name. For that matter, where’s the rest of the Crew? All four of them were in the room last time Die entered, his would-be partner unconscious on the carpet. It takes Die a moment to connect the dots, to realize why Boxcars is really here. “Are... are you the Gentleman of Discretion?” 

“That’d be me.” He doesn’t make any sudden moves, his eyes glancing at the gun and then back up at Die. As if anticipating the question on Die’s tongue, he gives him an answer. “You’ve been placing a lot of those ads, getting more specific about what you want. I didn’t realize they were for real though, not until we showed up at the last one.” 

Any embarrassment over being easily figured out is pushed aside when Boxcars drops that last little fact. He didn’t know that. “What did you think I was placing them for if I wasn’t looking for someone?” 

“Droog figured it was a drug deal or something.” Boxcars shrugs, like that’s a completely rational response for somebody to have. And... well, actually it is, all things considered. That also explains why Slick was so angry when they didn’t find anything in Die’s pockets other than a key and $20. 

“Well it’s not.” Die realizes he’s let the gun drop and brings it up again, making sure to aim for Boxcar’s centre of mass. “Well, since you’ve had your laugh, I’ll leave.”

“I ain’t here to laugh at you. You said you wanted somebody big all over.” He shrugs again; that’s Boxcars. There’s no ignoring how perfectly he fits the model of what Die wants.

“So you just so happened to pick my ad to reply to?” His hand tightens on the gun. 

“No, I picked it on purpose. I’ve been reading ‘em for a while now. You know what you want in bed. So do I.” Boxcars sounds convincing, even if Die is hesitant to believe anything coming out of his mouth. “Way I see it, this ain’t got nothing to do with our jobs, and we won’t be pulling punches when we meet outside of here.” 

“The last time we met in a hotel room, you broke my arm.” Stitch has easily fixed that, but it hadn’t stopped it from hurting when it happened, or hurting again when it finally was lined back up and forced to heal. Die doesn’t move from the doorway. “I like it rough, but not that rough.” 

“Nothing’s getting broken today. And I ain’t making your stay if you don’t want to. You can keep fishing until you find somebody like me. I’ll have to keep looking until I can find somebody who can keep their damn mouths shut too.” Boxcars takes a step toward Die, and it’s only his self-control that keeps him from firing a round into the center of his mass. “If you’re interested, step in. You can look around if you don’t trust me that nobody’s hiding in here but me, but you won’t find anything. But if you ain’t coming in, then you should leave.”

Die should leave. It’s the smart thing. Instead, he puts his gun away, hoping that if he’s fucked up that Stitch puts him together before it’s too late. He shuts the door and takes a few steps forward. Boxcars is big, and Die’s eyes drift down to his crotch, wondering if he’ll be the one who doesn’t turn out to be a liar. “Most of the men who answered were exaggerating about what they had in their pants.” 

“You wanna see it?” Boxcars rests his hands on the top of his pants. Die should take this opportunity to pull his gun but... instead he nods. Boxcars undoes his belt and shoves his pants down. Turns out that he was exactly as advertised. Die looks at Boxcar’s cock and takes a step forward, pausing as he tries to decide what he should do. Boxcars just chuckles. “Go ahead skinny, you can touch.” 

Die looks at Boxcar’s dick and shrugs his coat off, throwing it to the side and walking over. He kneels down in front of Boxcars to get a good look at it, his hands wrapping around his thick cock. “You’re the first guy who’s been as big as he said he was in his ad.” 

“Never saw any point in lying when I’ve already got more than enough.” Boxcars just grins down at him as Die starts stroking his cock. “What about you? Lemme see what you’re packing.” 

Die keeps one hand on Boxcars while the other slips down and undoes his pants. He gets his fly open enough to pull his cock out, letting Boxcars get a good look at it. Die’s more than a little pleased when he feels Boxcars start to harden up, and Die quickly follows him, stroking himself a few times. 

“How do you want to do this?” Boxcars asks him. 

“I’ll get you hard, then you fuck me until I come.” Die leans in, tasting the head of Boxcar’s cock. It’s good, but even better is the sound Boxcars makes, a low guttural groan. He pulls back, glancing up again. “You can come wherever you want as long as you give me a warning.” 

“Sounds fine to me. How about we start with that mouth of yours?” Boxcars settles his large hand on Die’s cheek. popping his thumb into Die’s mouth for a moment. Die drags his tongue over the shell before it slips out. He leans forward and slips Boxcar’s dick in, letting it fill his mouth. Boxcars is big, and Die finds that his cock hits the back of his throat a lot quicker than he thought it would. He tilts his head and it slides down his throat a little, Die holding his breath for as long as he can before pulling back to breathe. Boxcar’s big hand ends up on Die’s head and he groans, clearly impressed. “That’s fucking great. Should have known you’d have it in you to do that.” 

Die knows he’s good at this, and he does it well, both hands managing the base of Boxcar’s shaft and balls while the rest of his mouth goes to work on the head and shaft. It’s been a while since he’s had anyone this big, and he takes his time, savouring how heavy Boxcars is on his tongue, how thick he is and the way his cock pushes ever so slightly into the back of his throat. He also puts on a show, exaggerating as he moves up and down, eyes flicking up to meet Boxcar’s face. The hand on his head doesn’t push him down, not when Die’s more than willing to do that on his own. 

The head of Boxcar’s cock slides into Die’s throat and he swallows, keeping a close eye on how badly he needs to breath vs how much Boxcars likes it. It’s a thin line, and more than once, he barely pulls back in time to get a breath before choking. Die doesn’t mind though, not with the way Boxcars is grunting with appreciation, and not when he’s more than happy to have a cock this big to play with. His last few hookups were disappointing due to lying about what they had to offer. Having the real deal makes all the difference in the world. 

He slides Boxcars down as deep as he can go, feeling his throat ache slightly as the large cock pushes against the walls. It’s Boxcars who pulls him up this time, Die gasping for air and choking slightly as he does. Spit clings to Boxcar’s cock, and while Die pants, Boxcars carefully pushes Die’s hands away. “Not that I didn’t appreciate that, but if you want me to fuck you, then we’re going to need to slow down. Any more of that and I’ll cum right down your throat.” 

Die shivers a little at the thought. Another time maybe, or later if Boxcars sticks around. But he’s right, Die does want to be fucked. He resists the urge to give that big cock another suck and gets to his feet, starting on his shirt. The fear he originally felt when he walked in the door is gone, and he gets naked, shucking his clothing and kicking them to the side. He palms the lube out of his coat pocket and sets it on the beside table, watching as Boxcars takes care of himself. 

Boxcars finishes undressing, giving Die a real good look at him. He’s a big man, and solid big too, pure muscle and thick and wide everywhere somebody can be. Die wants nothing more than just to climb him the way you’d scale an oak tree. Instead, he sits on the bed, opening the jar and coating his fingers. “You want to watch?” 

“I want to help. Give me some.” He extends his hand, and Die watches his fingers as they barely make it into the mouth of the jar. Boxcars coats them and Die lays on his back, spreading his legs. The Dersite sets his free hand on Die’s ass, his thick fingers finding Die’s entrance. Die wipes his hand clean on the bedspread, biting his lip as the first thing pushes inside. He does his best to relax, even though right now he’s thrumming with anticipation. “How many fingers do you think I could fit in you?” 

“Three, maybe-” Die hisses, wanting to fuck himself on the finger inside of him. Boxcars has another finger slide in beside the first, starting to stretch Die out. His fingers are so thick and this is going faster than it does when it’s just Die taking care of himself. Three’s going to be a lot, but nothing Die can’t handle, especially not when he’s planning on having that cock inside of him. “Ah- fuck. More.” 

“Just a second.” Boxcar’s fingers spread and so does Die, fingers digging into the bedspread. He’s so hard, his cock jutting up, and Boxcars chuckles and wraps his free hand around it, stroking Die. Boxcars grins down at Die in a way that’s half terrifying but intensely arousing. “Look at you go. Mister Willing, you are exactly as you said you would be.” 

“A-as are you, Gentlemen Disgressi-aaahh!” Die twists as the third finger slides in, the feeling so intense that he can’t rightly decide if it’s pain or pleasure. Boxcars’ fingers gently move inside of Die, stretching him carefully. The way Boxcars is using his fingers is better than most of the cock he’s had in him. “That’s- that’s perfect.” 

“If you think this is good, just wait until I get the real deal inside of you.” Boxcars gives him another few pumps before sliding his hands out and off of Die, leaving him empty and desperate. “Which way do you want to do this skinny?” 

“Let’s start like this. I’ll tell you when I want to switch.” Die stays on his back, legs tucked up. Boxcars shifts in front of Die, rocking him up a little further. He gets a nice view of Boxcars lubing his cock up. To say he’s excited is an understatement. Boxcars might be part of the Midnight Crew, but he’s also got the best dick Die’s seen in ages. 

“Hup we go-” Boxcars presses his cock against Die’s ass, rubbing it against his cheeks a few times before pressing against the entrance. He’s big, and even with all the prepping, it still burns slightly as the head of his cock pushes in. It’s a good burn though, and he knows it’ll feel great once he gets used to it. Boxcars grunts as he carefully pushes in, his face scrunching up. “Fuck, you feel good.” 

“S-so do you.” He hooks one leg on Boxcar’s shoulder, the other quickly joining as he gets traction. Boxcars’s cock keeps sliding in and out of Die slowly, each thrust in going a little deeper than the last. Die’s hips tilt and turn to make it easier for Boxcars to get inside of him, and to make sure he goes in at just the right angle. 

If any of the Felt find out about this, Die’s going to be in some deep shit. Fucking guys gets him enough flack as-is, but fucking a member of the Midnight Crew? He knows exactly how that would blow over. Then again, Boxcars has just as much to lose as Die if Slick ever finds out. He might have even more to lose considering that the Felt at least has Scratch and Stitch around to keep anybody from murdering each other.

“More,” Die demands when Boxcars starts to hold back. He wants him in deep as he can comfortably go. The girth is testing him, but Die knows he can handle it. Boxcars chuckles and gives him what he asked for. It hurts in the best way something can hurt, and he moans, arching his back. “Good, keep it coming.” 

“You’re a greedy one.” He grins down at Die, reminding the part of him that’s a Felt that this is Boxcars and he could bite Die’s head off in half a second. But then those large hands squeeze Die as Boxcars slides in deeper and all he can think about it how good it feels. “I like that.” 

Die can’t help but laugh at that terrifying grin, his cock hard and bobbing slightly with each thrust. Boxcars is big and it takes time to get him in, until finally he finally bottoms out. They’re both breathing hard, and Die knows he’s not going to be able to sit down without some serious discomfort for at least two or three days. He’s so turned on that a few tugs could probably make him cum, his cock leaking a little against his belly. 

He’d like this to last a little longer though, and when Boxcars pulls back, Die motions for him to do it all the way. “S-switch.” The words come out in a pant, and when Boxcars pulls out, he’s left feeling uncomfortably empty. “On your- your back.” 

“If you want to do the work, I sure ain’t going to stop you.” Boxcars lies on his back and Die straddles him. The cock presses against his backside, wet and hard. He rubs up against it a few times, smiling when Boxcars groans. “C’mon skinny, don’t tease.” 

“This isn’t teasing. I can show you what that’s like if you really want me too.” He grinds down against Boxcars, then decides to get down to business before Boxcars remembers he’s bigger than Die, and he doesn’t have to take his shit. 

Die eases his way onto Boxcars, groaning as it stretches him out. He goes down as far as he can before stopping to breathe, his body squeezing tight. Then, he makes sure his knees are on a steady surface before popping himself up and down. Die picks a pace he can maintain, hands steady on Boxcar’s stomach while Die gets them both off. 

“I could watch you do this all day.” Boxcars is content to let Die do all the work. Die doesn’t mind, not when he’s got control of how each downward thrust will go, and he’s busy getting Boxcar’s cock to rub him just the right way. “Just keep on bouncing like that.” 

It’s hard to put a sentence together when he’s got the head of Boxcar’s cock nudging against his prostate. Die’s so used to being quiet at the Mansion that it takes him a while to really get into it, but his silent huffs slowly become steady moaning. Boxcars likes it, his fingers squeezing Die’s ass as it pops up and down. Die can only last so long, and he gives Boxcars another command, clenching tight around him. “Jerk me off.” 

One hand moves from his ass up to the front of his body, taking hold of Die’s cock. He doesn’t fuck around, squeezing and stroking him at a quick pace. Die quickens his own motion, fingers pressing against the carapace and trying to get a solid hold as he pushes himself to the limit. He feels like he’s going to pop like warm champagne, like his whole brain’s going to shut off. Die changes angles, letting Boxcars get him off while he slides that cock in deeper and deeper, until he’s nearly all the way down it. “Come on kid, you’re nearly there.” 

Die’s grunting by this point, desperate to come. Boxcars’ grip is firm and his cock is hard, but Die needs more. He grabs hold of Boxcar’s neck, trying to get that across to him. Somehow he gets it, and he just flips them over, tugging Die’s hips up and thrusting into him all the way. Die gasps and comes all over Boxcar’s stomach and part of his own, body arching against the bed and then collapsing a moment later. Boxcars is groaning too, his cock twitching hard inside of Die. 

He can barely feel anything below his waist, except for a constant warm glow of pleasure. But he does feel it when Boxcars pulls out and Die’s legs twitch at the sensation. “Where?” He manages to spit the question out, even as his body insists that now would be an excellent time to closes his eyes and sleep. 

“On your face.” The black and white-splattered torso looms over Die, a large hand closing over the slick cock and stroking it hard. Die reaches his own hand up, helping out as best he can. Boxcars drops his own hand and Die puts his other there, working both hands up and down the shaft. His face turns upward, over the expanse of chest to Boxcar’s face. Sweat’s rolling down his joints and he’s grimacing, nearly there. “Fuck, faster. C’mon skinny, I know you can- fuck! Do it!” 

Die wants to encourage him to come, but he’s still catching his breath. He focuses on stroking Boxcars as hard and fast as he can. Boxcars is so big, looming over Die and casting a shadow on him, and he’s breathing hard, so close that Die can nearly taste it. His mouth opens and he slips his tongue out, eyes darting up. And Boxcars looks down at Die with a hungry look. He comes a few seconds later, right over his face. Die closes his eyes, the cum landing on his cheeks and nose, and mostly right in his mouth. He lets it linger on his tongue before swallowing, his hands stroking Boxcars until nothing else comes out. 

The shadow over Die’s face disappears and he feels Boxcars sag down on the bed beside Die. Die tries to find something to wipe his face with, only to have Boxcars press some tissues into his hands. “There you go.” 

“Thanks.” Die cleans his face up, and then starts on the rest of his body, taking a moment to wipe down Boxcar’s stomach too. As he wipes, he can’t resist taking another touch, and he just holds Boxcar’s cock in his hands, feeling how heavy it is even while flaccid. “You were great.” 

“So were you. I didn’t expect much, but you were worth turning up for.” He sets a hand on Die’s ass, a few of his fingers pressing against Die’s entrance. Die’s already feeling sore but he doesn’t mind the attention. It’s nice. “You up for another round?” 

Die checks the clock then shakes his head. “I can’t. I want to, but I’ve got to head back before anybody notices I’ve gone. But... maybe another time? I’m free Thursday.” 

The fingers inside of Die push in a little further, stretching him until it burns, before relaxing and slipping out. “I can do Thursday. After lunch. I’ll get this room again.” 

“I’ll be there.” He reluctantly lets go of Boxcar’s cock, and they both get out of bed, putting their clothes back on. Boxcars leaves first, giving Die a pat on the ass before he slips out. Die waits ten minutes, carefully leaning against the wall. The drive back to the mansion is going to be hell, especially going over the bumps. But he doesn’t care. He finally met the Gentleman of Discretion he always wanted.

Maybe this will end badly. No, not maybe. Maybe suggests there’s a chance it won’t. It will end badly, that’s guaranteed. But he doesn’t care. Everything ends badly if you wait long enough. The least he can do is have fun while he’s still able to. And if Boxcars is up for it, then so is Die.

Die slips out of the room and heads for the car, whistling a little to himself. There’s another pre-written ad in an envelope in the car, waiting to be dropped off at the local newspaper, in anticipation of a disappointing encounter. Die tears it up and lets the pieces flutter out of his hands on the drive home.


End file.
